Anthraquinone dye and process of making same.



Unrrnn STATES PATENT OFFICE.

ROBERT E. SCHMIDT AND ANDREAS JAKGBI, OF ELBERFELD, GERMANY, AS- SIGNORS TO FARBENFABRIKEN OF EL'BERFELD 00., OF NEW YORK, N. Y.

ANTHHAQUINONE DYE AND PROCESS OF MAKING SAME.

forming part of Letters Patent No. 675,573, dated June 4, 1901. Application filed January 22, 1901. Serial No. 44,318. (No specimens.)

To a whom it may concern: amidoanthraquinones We can proceed, for in- Be it known that we, ROBERT E. SCHMIDT stance, as follows, the parts being by weight: and ANDREAS JAKOBI, doctors of philosophy, Ten parts of l.5-dichloro 4.8-dinitroanthrachemists, (assignors to the FARBENFABRIKEN quinone are mixed with one hundred parts 5 OF ELBERFELD COMPANY, of New York,) reof paratoluidin. This resulting mixture is siding at Elberfeld, Germany, have invented heated to about from 140 to 180 centigrade a new and useful Improvement in New Anuntil the melt has assumed a green color. thraquinone Dyes and Processes of Making The reaction mass is then poured into dilute Same; and we hereby declare the following to hydrochloric acid, by means of which opera- IO be a clear and exact description of our invention the condensation product is separated. tion. Subsequently it is dried and recrystallized Ourinvention relates to the manufacture of from pyridin. The resulting body, which new dyestuif sulfonic acids of the anthracene represents dark crystals, is soluble in anilin series by causing sulfonating agents to act on and in cold concentrated sulfuric acid with a 15 tetraalphylamidoanthraquinone derivatives green color and soluble in chloroform with a having the following general formula: bluish-green color. In order to transform NHR NHR this condensation product into the new dye- I I stuff sulfonic acid, ten parts of the finelypulverized compound are stirred into one 20 I I I I hundred parts of sulfuric monohydrate. The I I I resulting solution is then heated to about from 80 to 100 centigrade untll a test porf tion is clearly dissolved by water. Subse- NHR NHR, quently the reaction m ass is poured into about 25 (R meaning in this formula an alphyl radifrom one thousand to fifteen hundred parts cal, such as phenyl, tolyl, Xylyl, or the like.) of water. The dyestuff sulfonic acid thus The said anthraquinone derivatives can be produced, which is rather difficultly soluble obtained, for instance, by heating 1.5 or 1.8 in dilute acids, partially separates. The rest (lihalogen-alpha'dinitroanthraquinones havis precipitated by the addition of common salt.

0 ing the formulae: It is filtered off and dried. The sodium salt x o, l of the new dyestuff sulfonic acid thus obtained is, when dry and pulverized a dark powder, which is readily soluble in ivater and in am- I I I and I I monia with a green color. It is soluble with 35 I I I difficulty in hot alcohol with a greenish-blue I Baum) it is dissolved, yielding a greenish- 2 2 blue solution, the color of which is not (X meaning a halogen atom,) with primary changed on the addition of a small quantity 4o aromatic amins, such as anilin, paratoluidin, of ice, while on adding a larger quantity of Xylidin, or the like. The said dinitroanice the dyestuif sulfonic acid is separated in thraquinones can be produced by nitrating the shape of green flakes. the corresponding alpha-halogen anthraqui- The new coloring-matterdyes unmordanted 5 nones. and chrome-mordanted wool green shades. 45 The new dyestuif sull'onic acids obtainable The process proceeds in an analogous manby our new process are, in a dry state, dark ner if other of the above-defined alphylamipowders, which are soluble in water and in doanthraquinones are treated with sulfonatammonia,with from yellowish-green to greening agents. ish-blue color. They dye unmordanted and Having now described our invention and in 50 chrome-n1ordantedwoolfrom yellowish-green what manner the same is to be performed, to bluish-green shades. what we claim as new, and desire to secure by In order to produce the said tetraalphyl- Letters Patent, is-- color. By concentrated sulfuric acid (of 66 1. The process for producing new anthraquinone dyestuifs, which process consists in first treating 1. 4. 5.S-tetratlphylamidoanthraquinone derivatives having the following general formula:

NII IR I NHR action mixture, substantially as hereinbefore described.

2;'The process for producing a new anthraquinone dyestuff, which process consists in first treating 1.4.5.S-tetraparatoluidoanthraquinone having the formula:

with sulfonating agents, and then isolating the resulting dyestuff sulfonic acid from the reaction mixture, substantially as hereinbefore described.

3. The herein-described new anthraquinone dyestuffs, which, when dry and pulverized, are dark powders soluble in water and in ammonia with from yellowish-green to greenish-blue color, dyeing unmordanted and chrome-mordanted wool from yellowishgreen to bluish-green shades, substantially as hereinbefore described.

4. The herein-described new anthraquinone dyestuff obtainable by sulfonating 1.4.5.8-tetraparatoluidoanthraquinone, which dyestuff is, in the shape of its sodium salt, when dry and pulverized, a dark powder readily soluble in water and in ammonia with a green color, being soluble with difliculty in hot alcohol with a greenish-blue color, being dissolved by concentrated sulfuric acid (of 66 Baum) yielding a greenish-blue solution the color of which is not changed on the addition of a small quantity of ice, while on adding a larger quantity of ice the dyestuff sulfonic acid separates in the shape of green flakes; dyeing unmordanted and chrome-mordanted wool green shades. V

In testimony whereof we have signed our names in the presence of two subscribing witnesses.

ROBERT E. SCHMIDT, ANDREAS JAKOBI. Witnesses:

OTTO Kome, EDUARD FEBTIG. 

